Disruptive military officers like to pass around a quirky little book called Orbiting the Giant Hairball: A Corporate Fool’s Guide to Surviving with Grace by Gordon MacKenzie , who worked at Hallmark Cards for 30 years, carving out an identity as a renegade artist with the job title “Creative Paradox.” Using an eccentric combination of text, doodles, and other art, MacKenzie lays out a philosophy of rediscovering and employing one’s creative side within a stifling corporation.

I have made a career out of orbiting the giant Hairball of the U.S. Air Force. I have had the most unusual career of anyone I know in the military, mostly through deliberate decisions to avoid traditional career moves in favor of opportunities where I could breathe free air. Through all those assignments, my motivating purpose has been to develop novel ways to serve the Air Force and help it deal with the dynamic challenges posed by our national security environment.

Because I am such an oddball, I am often asked to mentor other oddballs. I am happy with the choices I have made, but orbiting the giant Hairball is not easy, and it is not for everybody.

Over the next few posts, I figured I would share a few of the lessons I have learned along the way. Although my lessons are specific to my Air Force experience, I think these lessons will broadly apply to anyone trying to achieve orbit in a corporate environment.

MacKenzie’s Metaphor

The Hairball, in MacKenzie’s view, represents the corporation. A Hairball has corporate gravity that draws all nearby mass into its tangled, impenetrable core. All that extra mass only increases its gravity, sucking everything into its “mass of Corporate Normalcy.” The Hairball embodies process, routine, precedent, norms, office politics, boredom, standardization—all the characteristics of Dilbert world that we love to hate.

The way for Creatives to survive, MacKenzie writes, is to launch into orbit. He is worth quoting at length here:

Orbiting is responsible creativity; vigorously exploring and operating beyond the Hairball of the corporate mind set, beyond ‘accepted models, patterns, or standards‘—all the while remaining connected to the spirit of the corporate mission.

To find Orbit around a corporate Hairball is to find a place of balance where you benefit from the physical, intellectual and philosophical resources of the organization without becoming entombed in the bureaucracy of the institution.

If you are interested (and it is not for everyone), you can achieve Orbit by finding the personal courage to be genuine and to take the best course of action to get the job done rather than following the pallid path of corporate appropriateness.

To be of optimum value to the corporate endeavor, you must invest enough individuality to counteract the pull of Corporate Gravity, but not so much that you escape that pull altogether. Just enough to stay out of the Hairball.

Through this measured assertion of your own uniqueness, it is possible to establish a dynamic relationship with the Hairball—to Orbit around the institutional mass. If you do this, you make an asset of the gravity in that it becomes a force that keeps you from flying out into the overwhelming nothingness of deep space.

This is a wonderful metaphor, because it gives equal importance to the creative impulse and the necessary pull of the organization’s mission. Freedom is not found through escape, but through service. This makes it a helpful framework for those who, either willingly or unwillingly, must seek their freedom within a large organization.

The metaphor is also helpful because it does not present a single right answer, but rather a dynamic tension. Most true things in life exhibit that kind of tension. As much as we would love to have clear-cut answers to life’s hardest dilemmas, life usually asks us–on an almost daily basis–to sit with our dilemmas, carefully consider the competing values involved, and find a situation-specific way forward.

The challenge of entering orbit

The first lesson I learned is that getting to orbit is not easy. It takes hard work and a great deal of luck, and not everybody finds a way to slip the surly bonds of earth.

Corporations do not like firing employees into orbit. Corporations are always resource-constrained, which means they want all hands on deck tackling urgent and important problems. Corporations also like their employees close at hand, where they can monitor them and ensure they are being productive. They only like to approve things with a high expected return on investment.

Permitting an employee to enter orbit runs against all of an organization’s instincts. The individual is, to some degree, beyond the reach of accountability. He or she is still drawing on the organization’s resources, still taking home a paycheck, but is not available for the organization’s most pressing lines of effort. The individual is doing… she is doing… hell, the corporation has no idea what she is doing. Her ROI is undefined. She is earning strange degrees in obscure subjects that have no immediate relevance to the corporate mission, or networking with communities that seem totally unrelated to its work, writing a book that she herself can’t explain after three years, trying to develop a product that nobody on the existing product teams quite understands. You can hardly blame the corporation for fretting over this.

When you are in orbit, you are detached and adrift. You spend a great deal of time exploring territory nobody has ever explored before, which means it takes a lot of time to even learn to ask the right questions. It involves many strange forays and serendipitous encounters before you can even hope to show your first results, let alone return to earth with a value-adding innovation. Worse, many of those pioneering astronauts will never really show ROI; every individual catapulted into orbit is a small bet, and we can only hope that enough bets pay off to justify the whole space program.

Entering orbit takes work

All of this means that the corporate overlords are right to be concerned. Letting any employee into corporate orbit takes tremendous trust. If you want to enter orbit, you have to earn that trust.

The U.S. military, for example, offers a wide range of off-the-beaten-path opportunities for extra education, cultural or corporate immersions, or other unusual assignments, but most of these programs are highly selective. To get in, you have to prove yourself a loyal and talented servant of the Hairball. In my case, I spent six years—ten, if you count the Academy—doing exactly what I was told, mastering my core profession of being an Air Force pilot, living at the heart of the Hairball, before I was accepted into an Olmsted scholarship to learn Arabic and move to Jordan.

Any time I have a mentoring conversation with a restless young professional who yearns for orbit, I start by telling them the same thing: before you even think about these unorthodox opportunities, focus on excelling in your primary career field. Cal Newport develops this idea in So Good They Can’t Ignore You, one of my favorite career development books. He argues against the conventional “follow your passion” model for finding meaningful work; instead, he argues for deliberately growing career capital through excellent performance, which ultimately allows you to gain more autonomy.

Even after you make that first foray into orbit, you will likely need to return to the Hairball from time to time to maintain your credibility, stay connected to the organizational mission, and report on what you have discovered. Upon my return from Jordan, I spent two years back in the Hairball, reestablishing my credentials, experience, and reputation in a flying squadron before I launched out into orbit again as a SAASS student and being selected to earn a PhD.

There is no right answer to how you should balance your time in the Hairball and your time in orbit; it is highly dependent on your organization, your personal situation, and your values and goals. In my next post, I will review a few different orbital trajectories.